Several years into my career as a school administrator, I led a schedule change that I was certain would be a triumph. We were moving to a block format, longer classes and fewer transitions. I had read the research. I had visited two schools that loved it. I presented it to the faculty with a confidence I had earned the hard way, and the vote was favorable. Nobody in the room, including me, asked a single question that began with the words, "What if this fails?"
It did not fail outright. It limped. The lunch schedule collided with the bus routes, the lab teachers had no way to fit a full experiment into the new blocks, and three of my best veterans quietly stopped trusting me. Every one of those problems was predictable. A tired custodian could have named two of them in the hallway if I had thought to ask. I had planned for success so thoroughly that I had never imagined the other thing.
The Funeral Before the Birth
Years later I came across a practice called the pre-mortem, developed by the psychologist Gary Klein and described in a 2007 article in the Harvard Business Review. The idea is almost embarrassingly simple. Before a project begins, the team gathers and imagines it is a year from now and the project has failed spectacularly. Then each person writes down the reasons why it failed. You do not ask whether it might fail. You assume it did, and you work backward.
The research behind it goes back to a 1989 study by Deborah Mitchell, Jay Russo, and Nancy Pennington on what they called prospective hindsight. They found that imagining an event has already happened increased people's ability to correctly identify reasons for the outcome by roughly 30 percent. The mind, it turns out, is better at explaining a catastrophe it believes is real than at predicting one it considers merely possible. Daniel Kahneman, who spent a career studying our overconfidence, called the pre-mortem one of his favorite techniques for exactly that reason.
"Begin each day by telling yourself: today I shall meet with interference, ingratitude, insolence, disloyalty, ill-will, and selfishness." — Marcus Aurelius, Meditations 2.1
The Stoics were doing this two thousand years ago. They called it premeditatio malorum, the premeditation of evils. Seneca wrote that the person who has rehearsed trouble in advance takes the blow with far less shock. It was not pessimism. It was preparation dressed as realism. Marcus Aurelius opened his mornings by listing the difficult people he would meet, not to sour his mood, but so that nothing would catch him off guard.
And long before the Stoics, a carpenter's son asked a question that is really a pre-mortem in a single paragraph:
"Which of you, desiring to build a tower, does not first sit down and count the cost, whether he has enough to complete it?" — Luke 14:28
Jesus did not say, "Build boldly and trust that it will all work out." He said sit down first. The book of Proverbs says the same thing in fewer words: "The prudent see danger and take refuge, but the simple keep going and pay the penalty" (Proverbs 22:3). Faith and foresight are not enemies. I confused them for most of my early career.
Why It Works When Planning Doesn't
The reason a pre-mortem catches what a normal planning meeting misses is mostly social. In an ordinary meeting, the leader has already announced a direction, and doubting it feels disloyal. The people with the best information, often the quietest, stay quiet. A pre-mortem flips the incentive. Spotting a flaw is now the assignment, and the person who finds the most plausible failure is the hero of the meeting rather than the troublemaker.
It also works against what psychologists call the planning fallacy, our stubborn habit of underestimating how long and how hard things will be. We fall in love with the plan. Once we are attached, we stop looking for evidence against it. The pre-mortem gives the skeptic in all of us a sanctioned seat at the table.
How I Run One Now
I use it for everything from a retreat I am planning to a major purchase to a conversation I dread. For a team project, I gather the group for thirty minutes and say, "Imagine it is one year from today. This effort has failed badly. Take five minutes of silence and write down every reason you can think of." Silence matters. If people talk first, the loudest voice sets the story. Then we go around the room, one reason per person, until every item is on the board. Finally we pick the three most likely or most damaging and decide what we will change in the plan because of them.
Last spring I did this with a small leadership group about a mentoring program we were launching. Within ten minutes, someone named a risk I had not seen: our volunteers would be enthusiastic in September and exhausted by February. We built in a pause and a replacement plan. In February, three volunteers needed that pause. I felt a quiet gratitude for a hypothetical funeral.
One caution. A pre-mortem is not a license for paralysis or for cynics to win every argument. The goal is not to kill the idea. The goal is to strengthen it. If the team finishes the exercise more afraid than when it started, the leader has run it badly. Done well, people leave with more confidence, because they have already met the dragons and sketched a plan for each.
You will find the full step-by-step in The Pre-Mortem on the tools page. It takes about thirty minutes and costs nothing.
Your Practical Takeaway
Think of one project, decision, or plan you are about to launch. Set a timer for five minutes and write, as though it already happened, a sentence beginning, "It failed because..." Write as many endings as you can. Circle the most likely one and ask what you could change this week to make it less likely. What failure are you not looking at because you are too attached to the plan?